JP2023507450A - ソルビタンエステルおよび酵素によるその製造方法 - Google Patents
ソルビタンエステルおよび酵素によるその製造方法 Download PDFInfo
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- JP2023507450A JP2023507450A JP2022537641A JP2022537641A JP2023507450A JP 2023507450 A JP2023507450 A JP 2023507450A JP 2022537641 A JP2022537641 A JP 2022537641A JP 2022537641 A JP2022537641 A JP 2022537641A JP 2023507450 A JP2023507450 A JP 2023507450A
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- Prior art keywords
- sorbitol
- carboxylic acid
- weight
- particularly preferably
- acid ester
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- -1 Sorbitan ester Chemical class 0.000 title claims abstract description 103
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 238000006911 enzymatic reaction Methods 0.000 title description 2
- 238000000034 method Methods 0.000 claims abstract description 80
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 146
- 239000000600 sorbitol Substances 0.000 claims description 146
- 239000000203 mixture Substances 0.000 claims description 59
- 108090001060 Lipase Proteins 0.000 claims description 45
- 102000004882 Lipase Human genes 0.000 claims description 45
- 239000004367 Lipase Substances 0.000 claims description 45
- 235000019421 lipase Nutrition 0.000 claims description 45
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 36
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 35
- 239000000194 fatty acid Substances 0.000 claims description 35
- 229930195729 fatty acid Natural products 0.000 claims description 35
- 125000002252 acyl group Chemical group 0.000 claims description 31
- 150000004665 fatty acids Chemical class 0.000 claims description 29
- 238000006243 chemical reaction Methods 0.000 claims description 26
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical group OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 claims description 21
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- KLDXJTOLSGUMSJ-JGWLITMVSA-N Isosorbide Chemical compound O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-JGWLITMVSA-N 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
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- MPCAJMNYNOGXPB-SLPGGIOYSA-N 1,5-anhydro-D-glucitol Chemical group OC[C@H]1OC[C@H](O)[C@@H](O)[C@@H]1O MPCAJMNYNOGXPB-SLPGGIOYSA-N 0.000 claims description 11
- MCHWWJLLPNDHGL-JGWLITMVSA-N (2s,3s,4s,5r)-2,5-bis(hydroxymethyl)oxolane-3,4-diol Chemical group OC[C@H]1O[C@@H](CO)[C@@H](O)[C@@H]1O MCHWWJLLPNDHGL-JGWLITMVSA-N 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 9
- 150000001413 amino acids Chemical class 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 150000001735 carboxylic acids Chemical class 0.000 claims description 6
- 230000032050 esterification Effects 0.000 claims description 6
- 238000005886 esterification reaction Methods 0.000 claims description 6
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- 241000228245 Aspergillus niger Species 0.000 claims description 2
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- 238000005260 corrosion Methods 0.000 claims description 2
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- 238000002360 preparation method Methods 0.000 abstract description 8
- 230000002255 enzymatic effect Effects 0.000 abstract description 6
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 74
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 64
- 239000002253 acid Substances 0.000 description 31
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 20
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 16
- 108090000790 Enzymes Proteins 0.000 description 16
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- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 16
- ZQPPMHVWECSIRJ-MDZDMXLPSA-N elaidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 description 16
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 16
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000005639 Lauric acid Substances 0.000 description 10
- 239000000523 sample Substances 0.000 description 9
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 8
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- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 8
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- 239000008117 stearic acid Substances 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- 239000007789 gas Substances 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical class OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 108010084311 Novozyme 435 Proteins 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 239000002537 cosmetic Substances 0.000 description 6
- 239000007857 degradation product Substances 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 150000005690 diesters Chemical class 0.000 description 5
- 238000000769 gas chromatography-flame ionisation detection Methods 0.000 description 5
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 5
- 229920005862 polyol Polymers 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 4
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 108010031797 Candida antarctica lipase B Proteins 0.000 description 4
- 108010093096 Immobilized Enzymes Proteins 0.000 description 4
- MSPCIZMDDUQPGJ-UHFFFAOYSA-N N-methyl-N-(trimethylsilyl)trifluoroacetamide Chemical compound C[Si](C)(C)N(C)C(=O)C(F)(F)F MSPCIZMDDUQPGJ-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- MBMBGCFOFBJSGT-KUBAVDMBSA-N all-cis-docosa-4,7,10,13,16,19-hexaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O MBMBGCFOFBJSGT-KUBAVDMBSA-N 0.000 description 4
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 4
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 4
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 4
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 4
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- 230000035484 reaction time Effects 0.000 description 4
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
- C12P7/6436—Fatty acid esters
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/14—Hydrolases (3)
- C12N9/16—Hydrolases (3) acting on ester bonds (3.1)
- C12N9/18—Carboxylic ester hydrolases (3.1.1)
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/14—Hydrolases (3)
- C12N9/16—Hydrolases (3) acting on ester bonds (3.1)
- C12N9/18—Carboxylic ester hydrolases (3.1.1)
- C12N9/20—Triglyceride splitting, e.g. by means of lipase
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- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/02—Monosaccharides
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- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/04—Polysaccharides, i.e. compounds containing more than five saccharide radicals attached to each other by glycosidic bonds
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
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- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/44—Preparation of O-glycosides, e.g. glucosides
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/62—Carboxylic acid esters
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
- C12P7/6436—Fatty acid esters
- C12P7/6445—Glycerides
- C12P7/6454—Glycerides by esterification
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E50/00—Technologies for the production of fuel of non-fossil origin
- Y02E50/10—Biofuels, e.g. bio-diesel
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- Life Sciences & Earth Sciences (AREA)
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- Medicinal Chemistry (AREA)
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- Biomedical Technology (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
- Detergent Compositions (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Enzymes And Modification Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| EP19218421.6A EP3839052A1 (de) | 2019-12-20 | 2019-12-20 | Verfahren zur enzymatischen herstellung von zucker-estern und/oder zuckeralkohol-estern |
| EP19218421.6 | 2019-12-20 | ||
| PCT/EP2020/086739 WO2021122973A1 (de) | 2019-12-20 | 2020-12-17 | Sorbitanester und verfahren zu ihrer enzymatischen herstellung |
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| JP2023507450A true JP2023507450A (ja) | 2023-02-22 |
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| JP2022537641A Pending JP2023507450A (ja) | 2019-12-20 | 2020-12-17 | ソルビタンエステルおよび酵素によるその製造方法 |
| JP2022537633A Pending JP2023507446A (ja) | 2019-12-20 | 2020-12-17 | 酵素による糖エステルおよび／または糖アルコールエステルの製造方法 |
| JP2022537637A Pending JP2023507448A (ja) | 2019-12-20 | 2020-12-17 | キシリトールカルボン酸エステルおよび酵素によるその製造方法 |
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| JP2022537633A Pending JP2023507446A (ja) | 2019-12-20 | 2020-12-17 | 酵素による糖エステルおよび／または糖アルコールエステルの製造方法 |
| JP2022537637A Pending JP2023507448A (ja) | 2019-12-20 | 2020-12-17 | キシリトールカルボン酸エステルおよび酵素によるその製造方法 |
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| US (3) | US20230033620A1 (pt) |
| EP (4) | EP3839052A1 (pt) |
| JP (3) | JP2023507450A (pt) |
| CN (3) | CN114787118A (pt) |
| BR (3) | BR112022011988A2 (pt) |
| WO (3) | WO2021122971A1 (pt) |
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| EP4355739A1 (en) | 2021-06-18 | 2024-04-24 | Evonik Operations GmbH | Compositions comprising n-nonanoic acid esters of xylitan and/or sorbitan |
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| GB947830A (en) * | 1961-06-20 | 1964-01-29 | Ledoga Spa | Esters of fatty acids with xylite |
| GB1016885A (en) * | 1962-10-16 | 1966-01-12 | Ledoga Spa | Xylitol esters |
| BE623684A (pt) * | 1962-10-19 | |||
| GB1025028A (en) * | 1962-12-28 | 1966-04-06 | Ledoga Spa | Xylitol esters |
| JPS58116688A (ja) * | 1981-12-28 | 1983-07-11 | Asahi Denka Kogyo Kk | 油脂類のエステル基交換反応方法 |
| US4614718A (en) | 1983-08-23 | 1986-09-30 | Dai-Ichio Kogyo Seiyaku Co., Ltd. | Synthesis of sugar or sugar-alcohol fatty acid esters |
| JPH0665309B2 (ja) | 1986-11-26 | 1994-08-24 | 花王株式会社 | エステル化方法 |
| EP0413307A1 (en) * | 1989-08-15 | 1991-02-20 | Lion Corporation | Process for producing saccharide fatty acid monoesters |
| DK144292D0 (da) | 1992-12-01 | 1992-12-01 | Novo Nordisk As | Forbedret fremgangsmaade |
| US5635614A (en) * | 1995-06-09 | 1997-06-03 | National Research Council Of Canada | Sugar/sugar alcohol esters |
| GB0409066D0 (en) | 2004-04-23 | 2004-05-26 | Ici Plc | Surfactant composition |
| CN101278047B (zh) | 2005-09-30 | 2012-12-12 | 诺维信公司 | 酶的固定化 |
| DE102009001748A1 (de) | 2009-03-23 | 2010-09-30 | Evonik Goldschmidt Gmbh | Formulierungen enthaltend Sorbitancarbonsäureester |
| KR101452769B1 (ko) * | 2012-09-25 | 2014-10-21 | 지준홍 | 지속성 냉감 효과를 갖는 자일리톨 지방산 에스테르를 유효성분으로 함유하는 화장료 조성물 |
| KR101939851B1 (ko) | 2013-10-01 | 2019-01-17 | 켐유니온 키미카 엘티디에이 | 화장품, 약제학 및 수의학 적용분야를 위한 항미생물, 공-유화제 및 증점제 특성을 가지는 자일리틸 에스테르 함유 조성물 |
| KR20150057589A (ko) * | 2013-11-20 | 2015-05-28 | 지준홍 | 자일리톨 지방산 에스테르를 유효성분으로 포함하는 방부제 조성물 |
| CN105754982B (zh) * | 2014-12-15 | 2021-12-07 | 丰益(上海)生物技术研发中心有限公司 | 固定化脂肪酶以及固定化脂肪酶的制备方法 |
| KR101823324B1 (ko) * | 2016-07-12 | 2018-03-14 | 주식회사 일신웰스 | 당 지방산 에스테르 제조방법 |
-
2019
- 2019-12-20 EP EP19218421.6A patent/EP3839052A1/de not_active Withdrawn
-
2020
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- 2020-12-17 WO PCT/EP2020/086736 patent/WO2021122971A1/de unknown
- 2020-12-17 JP JP2022537633A patent/JP2023507446A/ja active Pending
- 2020-12-17 CN CN202080086956.1A patent/CN114787118A/zh active Pending
- 2020-12-17 US US17/757,711 patent/US20230033620A1/en active Pending
- 2020-12-17 JP JP2022537637A patent/JP2023507448A/ja active Pending
- 2020-12-17 BR BR112022011988A patent/BR112022011988A2/pt unknown
- 2020-12-17 CN CN202080086950.4A patent/CN114787368A/zh active Pending
- 2020-12-17 EP EP20833826.9A patent/EP4077698A1/de active Pending
- 2020-12-17 BR BR112022011453A patent/BR112022011453A2/pt unknown
- 2020-12-17 WO PCT/EP2020/086739 patent/WO2021122973A1/de unknown
- 2020-12-17 EP EP20833824.4A patent/EP4077696A1/de active Pending
- 2020-12-17 US US17/757,528 patent/US20230023141A1/en active Pending
- 2020-12-17 WO PCT/EP2020/086737 patent/WO2021122972A1/de unknown
- 2020-12-17 CN CN202080086984.3A patent/CN114829617A/zh active Pending
- 2020-12-17 BR BR112022011457A patent/BR112022011457A2/pt unknown
- 2020-12-17 US US17/757,576 patent/US20230055814A1/en active Pending
- 2020-12-17 EP EP20833825.1A patent/EP4077697A1/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CN114787368A (zh) | 2022-07-22 |
| EP4077698A1 (de) | 2022-10-26 |
| BR112022011457A2 (pt) | 2022-08-23 |
| WO2021122972A1 (de) | 2021-06-24 |
| US20230055814A1 (en) | 2023-02-23 |
| WO2021122973A1 (de) | 2021-06-24 |
| EP4077696A1 (de) | 2022-10-26 |
| BR112022011988A2 (pt) | 2022-08-30 |
| CN114829617A (zh) | 2022-07-29 |
| WO2021122971A1 (de) | 2021-06-24 |
| EP3839052A1 (de) | 2021-06-23 |
| EP4077697A1 (de) | 2022-10-26 |
| JP2023507446A (ja) | 2023-02-22 |
| US20230023141A1 (en) | 2023-01-26 |
| US20230033620A1 (en) | 2023-02-02 |
| CN114787118A (zh) | 2022-07-22 |
| JP2023507448A (ja) | 2023-02-22 |
| BR112022011453A2 (pt) | 2022-08-23 |
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